The best part of traveling alone is that the pace, the topics, and what you see are entirely up to you, something some find daunting but I find exhilarating. The reality is that when you're traveling with another person, you have to keep up (or slow down) with that person, keeping in mind that they might be tired or might be desperate to see the next location. Frequently when I have traveled with people in the past I might really want to see a fourth museum that day, knowing that if we don't we'll probably never see it, but they are clearly tired or hungry and want to head back to the hotel. I'm someone who doesn't A) travel all that often and B) when I do travel, I'm likely to be going to that place only the one time as I'm not really someone who does "relaxing" vacations (I'm fully capable of relaxing at home), so I tend to do more "tourist-y" vacations (unless I'm going to NYC, which I do often). Going by yourself means that you travel without any pressure on your itinerary. Some days when I'm out by myself, I might only do one thing, then sneak back to the hotel and either go to the pool or even just have a nap on a bed that I didn't have to make. Other days I'll be up at dawn, not yet adjusted to the time zone shift, and be starting on my list of sites I want to visit or see right away. This is the best part of a trip by yourself-you get abject freedom to make decisions for yourself without having to worry about another human being. Even if you're single, you don't get to do this very often, and it can really help you get to know yourself and create an idea of what you actually like to do when you don't have the pressures of those around you dictating your decisions.
2. Become Comfortable With Your Own Skin
One thing that's a little intimidating about traveling alone is that you have to be comfortable spending time with yourself and only yourself. This can be a challenge for people who don't do this very often. I'm not going to lecture about safety and feeling safe by yourself (that's up to you and you know your limits better than I can dictate there), but instead about being by yourself and your thoughts. While I do tend to spend almost all of my free time by myself, this is not for everyone. When I was younger and most of my friends were single, they were never really "alone" during that time, always having regular significant others or roommates or families that they saw most nights of the week. It was a rare night that they were truly heading home, by themselves, no activities or dates scheduled for the evening.
This isn't the case for vacation. While people are generally pretty friendly, they're also on vacation, so unless you use a dating app for a meet-up, you're not going to be anyone's center-of-attention or the person that everyone wants to talk to, and that can be a challenge because it's not something many people are used to doing. If you're not sure if you like this, or can handle it, force yourself to go out to dinner at a restaurant alone, because you're probably going to do that on a vacation by yourself at least once. See how it feels to just have yourself and some activity (whether it's a magazine, your phone, a book, or just enjoying the meal) as company. Some people love this (I find it deeply therapeutic and I tend to enjoy my food more), but others find this to be a personal hell. If you can't handle the restaurant, you probably can't do this for a full trip. The one thing, I will say before you try this though is that no one is looking at you because you're by yourself. This is just something we convince ourselves is true, but really-no one pays attention to you in a restaurant by yourself. The only time you even acknowledge you don't have someone with you is the host or server asking you, and they genuinely don't care. Your service is the same, your food is just as good, and literally no one else in the restaurant notices you, unless by some chance they know you in real-life. So don't let that deter you.
That being said, going on vacation alone isn't without its faults, and perhaps the one you're going to notice the most is the couples. I would be lying if I said that I wanted to take all of my vacations alone (I don't actually take them all alone, but increasingly that's the course-of-action), but I don't have a romantic partner so this is one of the better options for me if I want to travel. If you go somewhere tourist-y, particularly a resort or beach-tilted vacation like the Bahamas or Napa Valley, you are going to see couples. Lots of them.
This can be triggering for some people, as most single people have at some point in their lives wanted that for themselves, and many people traveling alone want that for their lives still (I know I do). This can be particularly tough on a tour group; on my last vacation, I went on three tours, all of which I was the only person that was by myself (there were either couples, families, or friends on all of them), and it can be a bit of a challenge if you let it get to you. Tour groups are really nice in that you get to see a lot of a place very quickly and efficiently, and the other people in your tour will love you because you'll take pictures for them (and vice versa) as not everyone wants just selfies on their Instagram, but it can also be tough knowing that all of these people are with someone else and you're not. You won't escape the fact that you're single on a vacation, even if you get a better sense of what you want and who you are (I've gotten that every vacation I've ever taken). I don't want this to deter you, but I do want you to know that this doesn't go away-you are not Diane Lane, and you are not going to fall in love with some random handsome man who looks like he's on the cover of a Harlequin romance novel while you're out-and-about. But you still will probably have a magical time.
4. The Pre-Trip is the Worst Part
Here's where I think the worst part of traveling alone can come up: the pre-trip. When you're on vacation, honestly, other than if you're sensitive to couple-spotting or if you really don't like spending time with yourself, you generally don't care that you're by yourself. Hotels, airlines, restaurants, shopping-they want your money and you find quite quickly that they are more than willing to bend over backwards to help you out, making your stay as convenient as possible. Life is not a sitcom, and provided you do a little pre-work (print out boarding passes and confirmations, maybe create a Google Map of all of the places you want to see for easy navigation), you'll be fine and the stress will wash away pretty damn quickly.
But the pre-trip is when you're actually going to get judgment from people, and it will come in two forms. The first is the utter disbelief on people's faces when you're traveling alone. It's the same look I get from people when they realize that I go to movie theaters or restaurants alone. There is a moment when clearly they're judging you, the shock on their face impossible to deny, and then they try to dial back that shock because they realize how insanely rude they've just been, by then saying something somehow even ruder with "oh, no, that sounds great, I just could never do it." You will get a lot of this, especially the first time you go, and you need to be strong in your resolve that you're doing what's right for you. They'll get over it pretty quickly.
The second part you have to deal with is recommendations. Sometimes this can be helpful, particularly from people who know you, and this is hardly a problem just for people traveling alone. What's unique about recommendations from people when you're traveling alone is people tend to get a bit more offended when you don't take them. When you're with a spouse, it's easy to say "my husband doesn't like that kind of food," or "my buddy isn't really into hiking" and people tend to let it slide. But when you're by yourself, people take it as a personal affront if you don't go to the seven restaurants you recommended or if you don't go to the specific secluded beach. Particularly when you ignore a tourist-y recommendation (like you don't do a luau in Hawaii or you just take a picture from the harbor of the USS Constitution in Boston instead of actually touring the ship), people act as if you've made your entire trip pointless in the process of skipping this one thing. Don't give in to this-this vacation is for you, not for anyone else. Do what's right for your time off, not anyone else's. If it's important to you, you'll see it, but you spend so much of your life doing things for other people, be a little selfish when you're spending a large amount of money and your vacation time, and only do things that are important to you. Let other dictate your time when it's shared-this is about what you want.
I think one of the things I regret most about my twenties (and I have lot of regrets from this time period), is that I didn't travel more. And this wasn't because I didn't have the money, time, or yen to travel more. It was because I was saving trips to take with a man. I wanted to see all of these places as a couple, and because I'm more of a light sampler on vacations rather than someone who wants to go back to the same place over-and-over (unless it's NYC, but we've established that already), I didn't go traveling. In my twenties the only places I went were NYC or places I'd already been, and I regret that because that's time I'm never getting back.
The reality is that single people are programmed to assume that someone is going to come along and then the "couples portion" of your life will begin, and this is when the traveling will start. The problem here is that the couples portion of your life may be delayed, or may never come, and you don't get to have that time back. If traveling is something you want to do, you can always do it again with another person, and if you're lucky and you want that for yourself, a romantic partner. Orlando is a completely different experience with a couple, or later as a family. But saying you'll wait for a date you don't know will ever come is a foolish thing to dictate your life, and you will wish that you had taken more opportunities when you look back at your life. It's a tired maxim, but you rarely regret the chances you took, you more often wish you'd taken the chances you ignored. This is true of vacation. You only get one life, and it doesn't get lived backwards and you have no guarantees within it, so plan for yourself first, and if someone else wants to join your journey, you'll easily be able to make room.
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